Naomi Wheeless, the Global Head of Customer Success at Square

Square: The Management and Leadership Strategy You Need to Modernize Your Contact Center


Running a contact center is one of the most challenging processes for a company when offering a unique and positive customer experience. Contact centers are the bridge that connects your customers to your brand and allows them to feel engaged and heard.

So, what makes running one so difficult?

I talked to Naomi Wheeless, the Global Head of Customer Success at Square, about the management and leadership strategy required to modernize and run a customer-centric contact center. 

Square is a publicly traded company providing financial, payment, and marketing services for businesses. Their contact center lies at the heart of their customer success strategy. Here’s what Naomi had to say.

Managing a Large Team Can Be a Big Challenge

One of the most prevalent challenges of running a contact center  is managing a large group of employees who sit at the battlefront talking to your customers, listening to their concerns and feedback, and relaying it to management to inform strategy.

Naomi understands this challenge all too well. She runs a team of nearly 2000 employees spread across 13 countries globally and sits at a powerful position on the company’s board, informing strategy and customer success.

Naomi’s team works around the clock, 24/7, to meet the company’s customer experience needs and ensure customers have enjoyable contact and communication with the company.

You Need to Invest in a Hybrid Team and Agent Empowerment

One of the biggest questions I get from my audience interested in contact centers is how do you run a customer-centric one? Naomi narrows this down to a hybrid team consisting of highly experienced people within the organization and “external” talent and agent empowerment.

“I think being thoughtful of who you put in charge and where they come from, from a background perspective, is very important.” 

From Naomi’s perspective and experience, you should have a hybrid team of company veterans who’ve risen through the ranks and “outsider” talent allows industry expertise and fresh perspectives to mix and create better customer experiences via the contact centers.

Naomi also believes giving contact center  agents adequate empowerment is crucial. Contact centers understandably work under strict policies and procedures. However, under-empowering your contact center agents negatively impacts customer experience and makes the job less enjoyable for the agents.

Customers often have to be placed on hold or wait for somebody to get back to them because their request must be escalated to someone else who is empowered. This is not efficient or effective.

Square, within reason, ensures its contact center agents are adequately empowered to answer most customer questions, making the experience enjoyable, fast, and positive for both parties.

You Need to Invest in Technology and Remote Work

Modern contact centers are all about technology. That is one of the big key things at Square. 

Naomi Wheeless tells me that while most of the 2,000 employees under her management are contact center agents, she has a team of data scientists, engineers, data analytics, and machine learning experts who help tell the whole customer success and customer experience story.

With remote work becoming a big part of most business operations, Square operates its contact center fully remote. That means one agent might have a colleague on the other side of the world. 

For Square, the pros of such a setup outweigh the cons, and they’re among the few in the industry getting it right.

Maintaining healthy interpersonal relationships and developing a strong sense of pride in Square and what the company does is also something they’re continuously working to improve with their remote employees.

Square’s contact center is a model of what a modern customer-centric contact center should look like and the big roles AI, data science, and modern technology play in improving the customer experience, leadership, and strategy.


Blake Morgan is a customer experience futurist and the bestselling author of The Customer of the Future. For regular updates on customer experience, sign up for her weekly newsletter here.

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